Ah, the night before Thanksgiving—a blend of nostalgia, anticipation, and maybe a little anxiety, and hopefully a mini skirt. For many, it’s a chance to reconnect with old friends, share laughs over pumpkin spice espresso martini, and live in the familiarity of hometown memories. But what happens when you unexpectedly run into your ex at your favorite local bar? And suddenly, the night can feel a lot like “tis the damn season” by Taylor Swift. We got a question from one of our readers asking what the hell do you wear if you’re expecting (or planning) to run into an ex the night before thanksgiving, and while I’m definitely not in that position, I could think of a thing or two that I’d do if I was put in that scenario.
There’s something intoxicating about reliving old connections, especially surrounded by familiar faces and laughter. A chance encounter with an old flame can lead to heartfelt reminiscing. Who knows? It might just turn into a fun story to tell later. But if you’d rather keep things light, the key is to focus on your own happiness and how you want the night to feel. And for me, that always starts with my outfit. I’m never in the mood to rip my closet apart for the perfect outfit, but time and time again it keeps happening. So, three weeks in advance seems like enough time for us to plan your outfit that maybe just ends in covering half your bedroom floor with clothes, instead of the whole thing.
Your outfit can be a game changer. If you’re feeling nostalgic and playful, go for a vintage-inspired look with jeans and a cozy knit sweater that says, “I’m comfortable but I read vogue. (or havens.) Layer it with a blazer for that effortless vibe. If you want a boost of confidence, go for a leather skirt or pants with a tight turtleneck. This look is not just trendy; it’ll make you feel good. When it comes to your mindset, remember to keep it fun. Afterall, you’re probably headed out with your friends in the first place, so let that be the only thing in your mind going into it. And if fate brings you face-to-face with your ex, then take it as a sign. Share a laugh, clink your glasses, have a good time—no pressure, just genuine connection.
Ultimately, it’s all about the mindset you bring. If you run into your ex and it feels like a scene from a rom-com, live in it! Laugh, clink your glasses, and reminisce about the good times—no strings attached. And If the vibe isn’t right, it’s okay to walk away and have a girls night knowing that you’re in control of your own story.
The night before Thanksgiving for sure can be filled with unexpected twists, but you have the power to shape your experience. Whether it turns into a heartfelt reunion or a spirited night out with friends, how you approach it matters. So put on the outfit, adopt the mindset that serves you best, and remember: whatever happens, you’re the one controlling the night. And if you wind up calling him “babe for the weekend” Taylor Swift would be proud.